Tim Ch. 02

This story continues on from "Tim Ch 1 -- Tim & Jessica are forced to work as submissive sex slaves.". This chapter works as a stand-alone story.

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Miss Christensen sat down to do her monthly reports. Jessica had proved a great success. She was pretty, liked her sex and had adapted well to the discipline, taking her punishment without complaint. Clients loved her. Miss Christensen remembered she had been a call-girl in London, a good start but still some call-girls found it hard to adapt to the beatings and the requirements of being submissive. Mr Cartwright had a soft spot for Jessica; he would be pleased that she was doing well.

Miss Christensen was less sure about Tim. He was handsome, almost pretty, and so far he had served clients well. They liked his innocent androgynous looks and waif like body. But he had resisted initially and she was unsure if he had been properly broken. She felt there was a risk that he would rebel in future. If he did Miss Christensen had a simple plan; immediate and extreme pain. Not subtle but she had to ensure he knew that he was a whore, merely a rich lady's plaything and had a duty to obey. Miss Christensen vowed to break him, no matter what it took. She was confident that if she could train him, he would make an excellent submissive prostitute.

For the first couple of weeks she had not put Tim 'on the system', having decided to sell him as a 'teenage virgin' to selected well-heeled clients. She had her stylists go to work on him so as Tim appeared to be an eighteen year old. When a potential client was identified, he was brought into her office in a collar marked 'virgin' and some brief black knickers. A member of staff posed as his mother who explained that Tim wanted to work as a prostitute and she was not going to stand in his way. He was fully trained and understood the punishments he would have to endure and the sexual services he would have to provide. She only asked that as his first date, the customer would be gentle with the poor boy and make allowances for his inexperience. She ruffled the hair and patted the thigh of her seemingly nervous (and almost naked) 'son'. Miss Christensen managed to charge a number of clients super-premium rates for taking his 'virginity'. Tim seemed to act the enthusiastic, naïve boy extremely well and clients were overjoyed with the experience. Soon he was 'on the system' and earning his keep as one of the junior whores.

After Tim and Jessica had been on the island for about a month, Miss Christensen announced, at one of her routine weekly briefings, that the next 'school' party would be the following month. This announcement seemed to cause great excitement. They were quickly filled in on the details. The island hosted such parties four times a year. They involved all the whores dressing up as schoolboys and schoolgirls and the whole island being transformed into a school. Most of the whores were in their early twenties and made no attempt to appear younger, the attraction was the outrageously sexy uniforms and the party atmosphere. The events were hugely popular with the clients, which made them very lucrative. The demand was such that Cartwright & Palmer imported whores in from other offices, mainly London and New York, to cater for the demand.

As the date came closer Tim was required to help with the preparations. This mainly involved converting some of the dungeons into school rooms and opening up the bespoke school buildings; these housed the showers, dormitories and changing rooms.

A week before the first guests arrived everyone was issued with their uniforms. Both boys and girls were to wear white satin shirts buttoned at the wrist and neck along with a dark blue striped tie with the colour of the stripe indicating the whore's grade. Girls wore a very short black satin pleated skirt and the boys tight black satin shorts. The only non-school item of clothing was lingerie, they were all permitted to wear their normal knickers.

Everyone was photographed for the 'yearbook' (available on-line or for $85 at the island's shop). The top of the page was pretty standard; the girl or boy in their school uniform, their age, statistics, grade, orientation (about 95% said bi-sexual) and education (there were a number of degrees and even two doctorates on the staff). The bottom of the page was less conventional as it had photographs of the person naked along with the sexual services they offered.

Tim had already been photographed for his web page. Shots had been taken fully clothed, in swimwear and a couple of shots of him naked lying on a fur rug showing his delectable bottom; all quite tame. For the school photographs Cartwright & Palmer brought in their official photographer, 'Chiara Salvadori'. Tim dressed in his school uniform and presented himself at one of the dungeons that had been transformed into a studio for a few days. Chiara was a slim beautiful woman, probably in her mid to late thirties, with her dark hair swept back in a pony tail. She certainly had a presence and a natural authority that Tim found slightly surprising in view of her slight physique.

"Tim, let's start with you leaning against the wall ... pull up your shorts I want them to look tight." Chiara took shots from various angles of him in his uniform. "OK, shirt off ... arms across your chest ... smile ... bend over ... kneel ... up you get ... now take your shorts down ... slowly."

Tim was now down to his brief black knickers, "Good, let's start with your arms across your chest ... now, hands behind your back ... turn around, and bend over ... kneel down, hands in front of you ... eyes down, look embarrassed ... lay down on the bed ... and pull your pants down just a little ... thank you."

Chiara handed Tim a pot of cream and told him to cover himself with it. She said it would stop his skin reflecting the bright photographic lights. Initially he rubbed some on his face then his arms, and gradually went down his body, missing his pubic area. Tim began to enjoy massaging himself, although he would have liked some privacy. He did his back and finally his bottom. Chiara warned him he had to do all his body, as any bits he missed would reflect the light. Taking the hint, Tim turned away from Chiara as he rubbed it into his penis and between his legs. Looking down he saw he had a huge erection, the cream made his skin tingle, it was a very erotic feeling. Tim gave himself a last once-over to ensure he was really complete, he was enjoying this. Chiara was enjoying taking the photographs. She knew the cream would get him very aroused, so he would loose any inhibitions he might normally have. It should make it much easier to get him posing in the nude and to agree to some pretty explicit scenes she had in mind.

Chiara took photos of Tim naked from the front, then back. She then had him coyly trying to cover himself with his knickers, bending over, pulling his buttocks apart, in 'the position', on his back with his legs spread and finally on all fours. Most of the poses she wanted Tim to be relaxed, but sometimes she had him erect. Tim simply obeyed, smiling depending on Chiara's instructions. He had been under Cartwright & Palmer discipline long enough to know not to complain, anyway he was rather enjoying it.

"Now for the fun. Get on all fours ... let's start with the dildo ... please insert it." Chiara handed Tim a large black dildo and tub of lube. Tim did as he was told despite the dildo being considerably bigger than he was used to, and eventually he inserted it to Chiara's satisfaction. Chiara photographed him on his hands and knees then lying on his back playing with the dildo. All the time Chiara was giving Tim instructions, "Come on try harder. Tim I want to see that dildo all the way up." Tim was sweating as he tried to get the dildo into his anus, it was really huge, he would like to see Chiara do this. "Keep yourself erect ... keep pumping ... faster ... I want a look of ecstasy ... legs wider, really spreads those legs ... now I want some close ups of you sucking the dildo ... deeper ... perfect."

Tim knew things were getting a little heavy but was feeling hugely horny so was happy to follow Chiara's instructions. "Susan your turn now." A pretty naked girl walked over. Tim had never met her and it seemed they were going to do a photo shoot without being formally introduced. They started with them in an intimate embrace but quickly moved to sex, first in the missionary position, followed by doggie. Any thought of simulating it had long been forgotten. Chiara wanted it 'hard and dirty'. She had Tim lie on his back as Susan gave him an (excellent) blow job. Finally she had Tim lick Susan's pussy. All the time Chiara was taking photos from all angles.

"Tim almost done, we just need you to pose with on the St Andrew's cross and a few other bits of equipment." Chiara buckled him onto the cross, and took photographs of him from the front. She then turned him around and secured him. The restraints were tight and Tim couldn't relax. When fully secure, Chiara picked up an old fashioned cane and hit Tim four hard strokes on the buttocks. "Tim, sorry about that, but the stripes across your arse look wonderful." Susan returned, now dressed in PVC underwear, suspenders and boots. She posed spanking Tim over her knee, standing on him and whipping him with a riding crop. Lastly Chiara had Tim kneeling licking Susan's boots.

Tim was tired and felt abused when he was finally released. Chiara seemed to enjoy ordering him around stark naked and intentionally humiliating him, by the end she was calling him 'slut'. He thought she must have taken hundreds of shots; she could produce an entire pornographic book rather than 'a couple of shots for the website' as she claimed. Even so, Chiara told Tim she wanted more, he was to be at the 'Kusiemski pool' at 11am the next day for the outside shots.

Tim presented himself as ordered. Chiara got Tim to strip and massage his skin with coconut oil so it was glistening. She recorded Tim's progress. She then took shots of him in his bikini lying down, back and front. She got him to untie the sides and took shots where Tim was covered but only just, he was meant to look very 'available'. She took some photographs of him walking by the pool, swimming and in particular just getting out of the pool. She repeated this process with Tim wearing a tiny pair of trunks and finally naked. She took a lot of photographs of him naked; lying on his front and back on the lounger, spreading his legs and kneeling on the lounger showing off his pert bottom. Then walking by the pool, casually carrying a bikini and finally more photos of him swimming. By the end of the session Tim had quite an audience that Chiara did nothing to discourage. The next day Tim arranged to see Chiara. He was embarrassed as he felt the first session in particular was very explicit. He shuddered when he remembered some of the poses he had been in. What had he been thinking? He hoped he could persuade Chiara to junk some of the most salacious shots. This said, he knew some good photographs could lead to a great increase in the 'dates' he was booked for. Chiara showed Tim the selection she had chosen for his web page with some pride, but declined to remove any, despite Tim's entreaties. ~ The first yachts started arriving on the Wednesday evening but most of the guests arrived on Thursday when management provided an efficient shuttle service from a couple of private landing stages on the mainland. All guests were met by a whore who carried their luggage and made sure they were comfortable and if they were new to the island showed them around the resort.

Tim had been booked for the initial date by a lady called Christin von Eberstein. He was told she was to be arriving at 11am on Thursday and he should present himself at the marina to greet her. As the booking had been made well in advance Tim had the opportunity to ask around to find out about this Eberstein. He was told she was a beautiful German lady. When she was in a good mood she could be quite charming when irritated she could be a complete bitch, taking great pleasure in humiliating her whore and causing them great pain. She demanded constant attention and respect.

The meet up was easy as Christin had seen Tim's photographs. Tim was keen to make a good initial impression so immediately dropped to his knees. He then carried Christin's luggage to the hotel complex.

Whilst Tim unpacked Christin's things, Christin went out on the balcony to admire the view. Although nothing had been said, Tim could feel the massive sexual tension. When she thought Tim was not looking Christin rubbed herself producing a rather attractive soft pink flush.

"Tim, the position."

Tim stripped naked and got down on his knees, it was important to get off to a good start especially for these longer dates. After all he had been warned not to take any liberties.

"Tim, I have been to the island on several occasions, but this is the first time I have managed to make one of your Schoolboy parties. We have a school room booked for 3pm, before then I want you to take me around and show me the 'sights'."

Tim started his tour with the games rooms. There was a girls' basketball game being played. The girls wore very revealing outfits. Tim explained that their outfits all had their personal number on them in the same way that girls' uniform skirts and boys' shorts did. So if a client liked the look of one of the players they could be booked. Christin was interested and seemed to have eyes for a tall Brazilian playing in defence, her lithe frame hid a formidable physique.

Tim then showed Christin the gym. As well as the normal weights machines and treadmills there was an area where they saw a number of female whores practicing their floor exercises. It always amazed Tim seeing how flexible some of these girls were. He saw one girl doing a slow perfect splits. All the girls had their numbers embroidered on their leotards. Tim showed Christin a keypad so that observers could summon any of the whores they liked the look of. Keying in the number 20 Christin sent for a girl called Nadia. Nadia seeing her number immediately stopped her exercise and rushed over, falling on her knees before Christin. Nadia was a professional athlete before she came to Cartwright & Palmer, representing Russia at the Beijing Olympic Games. She had continued with her punishing exercise schedule and Tim thought she had the most perfect body he had ever seen.

"Yes Miss, what can I do for you?"

"Let me see you in 'the position'"

Nadia stripped off her leotard and got back to her knees. Christin then asked her to stand up and turn around. Nadia did as asked, moving with her normal air of serenity. After turning around she did a slow back flip, showing her grace and athleticism, after which she returned to 'the position'. Christin evidently liked what she saw as she left determined to book the girl.

Tim escorted Christin to one of the resort's restaurants. As they waited to be seated Christin said, "Tim, lick my shoes." Tim got to his knees and started licking. Christin liked to do this sort of thing for many reasons; the first was the simple pleasure of humiliating Tim in public, then of course it showed Tim that she might treat him as an equal but that he should never forget his real status and lastly she could see how quickly the whore got to their knees. If there was some resistance or hesitation Christin knew that she the whore was probably second rate and she would have to start any session with severe corporal punishment to get the obedience she wanted. Tim passed the test.

When they were seated, Christin wanted to know about life on the island and how Tim found being a prostitute. She had looked at his web page and asked about some of the sexual services he offered, many of which were totally new to her. Tim gave Christin a 'sugar coated' version of life. To be truthful he didn't really know how he felt about his new profession, but he thought the situation called for light banter and a few amusing 'war stories' rather than an in depth confession.

As they were drinking their coffee Christin handed Tim a pair of knickers and told him to put them on. Tim went to the back of the restaurant and changed, he struggled out of his shorts and then proceeded to put on the knickers. They were red with some subtle black lace trim. The difficulty was they were made of satin, lovely and smooth but with very little 'give', eventually he got himself into them and returned. Christin felt that these knickers were the best mementos of a successful date. She just loved wearing them later, remembering the fun she had had. She was wearing some pink ones that had been worn by a poor girl in London called Marie-Louise. Helen had told her that the girl liked it 'rough' and 'really enjoys pain'. Christin had spent a wonderful afternoon humiliating her. Christin remembered whipping her and forcing her to put ever larger dildos into her pussy and bottom. The girl could barely stand by the end of it. Marie-Louise must have been one of the most depraved tarts on the firm's books, she seemed to have no limits. Christin smiled as she remembered Marie-Louise dressed just in the knickers drinking from a dog bowl in the bar and how she ordered the poor exhausted slut to go to a neighbouring table and offer herself free of charge. The last Christin saw of the girl was her being led away stark naked by four men, doubtless to be rogered senseless. Oh how she enjoyed wearing these knickers and hoped the red ones would bring back similar memories.

After lunch, Christin sent Tim off to check the school room's number. She leant back and stared at his bottom, so beautiful in those tight satin shorts. She mused that there were a number of other agencies that could provide boys and girls as attractive as Cartwright & Palmer, but it was a submissiveness and willingness to please that really made these whores stand out. She knew that Tim would comply with any of her orders, no matter what they were, no ifs or buts he would simply do it. She could see that sometimes a whore might be deeply humiliated or in great pain but a Cartwright & Palmer prostitute never refused. Christin loved this obedience and was prepared to pay handsomely for it. The island seemed even better than Regensburg or London.

As she cradled her wine she thought of what she was going to do to Tim. She had read the sexual services he offered and as ever was amazed and the number and variety. Over the past couple of weeks she had filled every waking hour with one erotic idea after the next, the list was endless. Now she had seen that Brazilian and that minx Nadia. What a wonderful thought, these two doing anything she wanted. Which should she take? A lovely dilemma.

After lunch they went to Cartwright & Palmer's shop. This huge room was in the basement of the hotel and about two thirds of the area was given over to various sexual aides, the rest to DVDs and magazines. Christin bought a couple of DVDs of Tim being tortured and humiliated by two of the in-house dominatrixes. She then looked through the clothes and chose a PVC corset and a tight wet-look skirt for herself. She bought Tim the sweetest little satin sailors outfit and a brief gold spandex bikini. She longed to see his embarrassment as she forced him to wear it by the pool.

They walked to the whips section, the choice was incredible. "OK, Tim bend over I want to test a few of these." Tim bent over as he was told.

"Oh come on Tim, shorts down." Tim wriggled out of his shorts and then acknowledging the inevitable took down his knickers. Christin practiced using a paddle then an old fashioned cane. Tim winced as the cane struck his buttocks, looking around he saw he had quite an audience. Eventually Christin decided on a cat and a cane.